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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: zeoblade on May 20, 2011, 10:13:26 PM

Title: Oxidation of I2 to I+ with HNO3
Post by: zeoblade on May 20, 2011, 10:13:26 PM

I2 + HNO3 --> I+

Where can you find the mechanism to oxidise I2 to I+ with HNO3?

Title: Re: Oxidation of I2 to I+ with HNO3
Post by: Schrödinger on May 21, 2011, 02:29:15 AM

I know that HNO3 oxidizes I^- to I₂ and I₂ to I⁵⁺.. But I've never heard of this one. Does this reaction actually happen or is it a theoretical question?

Well, if the reaction really does occur, please forgive me for my ignorance.

Title: Re: Oxidation of I2 to I+ with HNO3
Post by: zeoblade on May 21, 2011, 02:34:59 AM

It says in a textbook that if you want to electrophilically substitute benzene with I, it has to be an electrophile.

To be an electrophile I₂ should be I⁺ so maybe I⁵⁺ is the electrophile.

The textbook says that I₂ with an oxidant such as HNO₃ can make I⁺

I'll go look in Vogel after the weekend, appreciate your direction

Title: Re: Oxidation of I2 to I+ with HNO3
Post by: Honclbrif on May 21, 2011, 11:58:49 AM

I believe ICl can act as a source of I⁺. Don't know if it will modify benzene though. I'd recommend a Sandmeyer with KI for that.

Title: Re: Oxidation of I2 to I+ with HNO3
Post by: nox on May 22, 2011, 02:51:13 AM

I think "I⁺" is really an idealized formalism to indicate an electrophilic iodine species. I do not believe an actual I⁺ species exist, it probably exists as some sort of charged complex, much in the same vein H⁺.